


Riding To Heaven And Back

by PunkWithFlowerCrowns



Series: Heating It Up [3]
Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Barebacking, Bottom Jackson Whittemore, Dom Isaac, Dry Orgasm, Hurt Jackson, Insecure Jackson, Isaac Doesn't Know Jackson Is His Mate, Isaac Likes Jackson's Penis, Jackson Does, M/M, Mentions Of Stiles Topping Derek, Porn with Feelings, Prostate Milking, Riding, Rimming, Shameless Smut, Small Penis, Sub Jackson Whittemore, Top Isaac Lahey, Worried Derek
Language: English
Status: Completed
Published: 2014-07-29
Updated: 2014-07-29
Packaged: 2018-02-10 22:14:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,527
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2042202
Author URL: https://archiveofourown.org/users/PunkWithFlowerCrowns/pseuds/PunkWithFlowerCrowns
Summary: <blockquote class="userstuff">
              <p>Isaac finds someone else to touch than Stiles. </p><p>Jackson is happy for getting to please his mate but how long will it last when it's possible that Isaac doesn't even notice them being mates?</p><p>Derek is worried and Stiles is laughing his ass off.</p>
            </blockquote>





	Riding To Heaven And Back

“You want me to find someone else to touch, Jacks?” Isaac growled seductively in his ear, which sent shivers to Jackson’s spine. He was still pinned on the wall by Isaac, who was now smirking in front of his face. 

“I-Isaac? What the hell, man! Let me go!” Jackson growled. There was no way he was going to be dominated someone like Isaac who was the puppy of the pack. He was the dominating one, always.

“You wanted me to find someone else to touch. Found him,” Isaac said licking his cheek, “You’re going to beg so prettily for my cock, Jackson.”

“When the hell did you get so horny? And what’s with the dirty talk, I thought you were the innocent one in the pack?” Jackson was confused. Isaac had always been the shy one.

“Since I saw my Alpha fucking his mate. I want that to myself,” Isaac whispered, being more like himself when he looked vulnerable. Jackson looked at his pack mate and wondered how Isaac couldn't see it. Jackson had known for months Isaac to be his mate but he didn't say anything because Derek had said Isaac would notice if he felt the same. So he had waited, hurting so _fucking_ much when Isaac had been hanging with McCall not noticing him even once. 

“If you want to feel the same, you should find your mate to have sex with,” Jackson said and Isaac seemed to think about that for a second, “I guess, but at the moment you’ll be good enough.” Jackson whimpered. Good enough? He was just good enough for now, until Isaac would actually find someone else? He shook his head, it didn't matter. If he could spend this moment with his mate, he would take it, no matter how much it hurt afterwards.

“Yeah, okay,” Jackson pulled Isaac to a bruising kiss, to which Isaac immediately answered by kissing back and pushing Jackson towards the bed. He started shredding Jackson clothes off until he stopped him, 

“Calm down and take it easy, yeah? We’re not in a hurry, ‘saac,” Jackson whispered and Isaac slowed down, nodding himself. He laid Jackson down to the bad on his back, finally getting his trousers and boxers of with one go. Jackson’s cock sprung free and just look at that. He clearly wasn't so bad boy anymore. 

“Stop staring, Isaac. I know it’s… It’s…” Jackson started, looking embarrassed as hell. 

“ _Beautiful_ ,” Isaac cut him off, looking down at the cock which was two times smaller than his own. “Holy shit, that’s fucking adorable,” Isaac breathed out. Jackson couldn't be more embarrassed. 

“Just stop fucking looking at it. It’s awkward. Do you still want to…?” 

“Fuck, of course. So fucking hot, Jacks.” Isaac gave it a tentative lick and Jackson moaned. Isaac licked his cock few more times before taking it to his mouth. He smirked around his cock and took him deeper actually getting Jackson’s balls in his mouth as well. He sucked hard which made Jackson scream out loud and letting out little whimpers. 

“You like it? Do you want more?” Isaac asked after letting Jackson’s cock slip out from his mouth. Jackson nodded frantically, his face flushed and lips wet and red from biting them. 

“Beg for it,” Isaac whispered biting his inner thigh gently. Jackson looked at him confused.

“What?”

“Beg for it, Jackson or I’ll stop.” Jackson shook his head, afraid Isaac would really stop. 

“No! No, please, Isaac. I need more. I’ll be good for you, please, please, please. I’ll make it good for you, I promise,” Jackson begged and Isaac smiled, noticing that he would probably never get tired of hearing Jackson beg so prettily. 

“I know you will, love,” Jackson’s heart fluttered from the ‘love’. Isaac smiled and took off his own clothes before settling back between Jackson’s legs. Slowly, he traced his finger to Jackson’s puckered hole and circle it. 

“Too dry,” Jackson whimpered and Isaac nodded, “I know, just be patient.”

Isaac gave a long lick from his crack all the way to his balls, pressing his tongue down hard when he came in contact with Jackson’s hole. 

“Holy shit, Isaac! Again, please!” Isaac chuckled and licked over his hole, making it wet and pressed his tongue inside making Jackson moan lowly. Isaac wet his fingers and pressed one to his hole, which sucked his finger right to the knuckle. 

“Relax, babe,” Isaac said when he heard Jackson whimpering from the intruder. He pulled his finger out slowly before calmly pushing it back in, continuing to do this for a while. He added a second finger and started scissoring them, stretching Jackson’s hole for his cock. 

Jackson moaned loudly when Isaac found his prostate, constantly jabbing his fingers against it, “Isaac. Isaac? I’m gonna cum soon, if you don’t stop,” Jackson whimpered and all he got was an evil smirk from his mate.

“I know.” Isaac pressed his fingers to his prostate, slowly massaging it and Jackson couldn't help but scream from pleasure when his cock started leaking cum. 

“Wh… What?” Jackson looked down, seeing his cock leaking cum without stopping. Isaac chuckled to his inexperience, “I’m milking your prostate. You’re gonna come so much you’ll be dry and then I’ll fuck you.” 

“Fuck, please Isaac,” Jackson moaned. It was after a minute when Jackson finally stopped coming. He was panting and on his stomach was a large puddle of semen, which Isaac wiped off with a washcloth. 

“Are you ready?” Isaac asked and Jackson was quiet, “Are you ready, Jackson, I’m not going to ask again.” Jackson’s cock laid softly on his thigh and Jackson yelled from over-sensitiveness, when Isaac tug it gently. 

“Yes! Yes, I’m ready, please.” Jackson was so relaxed after the milking that Isaac could just slide in him easily, “Oh God, Jackson! You feel so fucking amazing.” He started slowly thrusting in and out of him, Jackson letting out little whimpers when his cock tried to grow hard again but couldn't. He loved how his mate’s cock felt inside him, filling him thoroughly. 

“Harder, ‘saac!” He screamed and Isaac obeyed him, starting thrust into him harder and faster until he stopped, making Jackson cry out from frustration. 

“I want you to ride me, Jacks,” Isaac said and laid on his back, helping Jackson to straddle him. Jackson took Isaac’s cock in his hand and placed it against his entrance before sinking down on it hard, making both of them moan simultaneously. Jackson placed his hands over Isaac’s chest, starting to ride him up and down fast. Isaac was moaning, holding Jackson’s waist, rubbing his thump across the smooth skin.  
He started thrusting back against Jackson and their moans grew louder as they both started to reach their orgasms. 

Jackson was first to come with a shout of Isaac’s name, his rim tightened around Isaac’s cock but nothing came out of his cock since Isaac had already milked him dry earlier. Just little droplets of come dripped on Isaac’s stomach. 

“Fuck, so tight…” Isaac mumbled, thrusting now slowly but hard, Jackson’s orgasm triggering his own. With one final push he came inside Jackson hard and he can happily admit that it was the best orgasm he had ever had. 

Isaac yawned, “That was amazing. I mean holy shit, Jackson, you’re amazing.” He looked down and saw Jackson had already fell asleep on his chest, Isaac’s cock still inside him. 

Isaac chuckled, wiping Jackson’s hair away from his forehead. 

~~~~

“Well, they certainly are loud,” Stiles laughed and looked at Derek. They were still lying in the bed and to be honest, Stiles didn't want to get out of the bed. Ever. He was so sore and his legs felt weak but he was also happy when he finally get to have Derek, who was actually looking worried at the moment. 

“What? What’s going on?” Stiles asked, “Are you worried about Isaac? Because I’m sure Jackson will go easy on him.” 

Derek shook his head, “I’m not worried about Isaac, Stiles. I’m worried about Jackson.” Stiles chuckled, “Why in the world would you be worried about _Jackson _?”__

__“I’m afraid Isaac will break his heart, when he doesn't notice Jackson is his mate. I’m glad Isaac isn't able to knot, because that would be one hell of a mess.”_ _

__Stiles eyes widened, “They’re mates?! Holy shit! This is amazing! What do you mean he might not notice it? Of course he will!” Stiles was excited but then his smile faded, “What do you mean ‘Isaac isn't able to knot’? Are you saying…” Stiles let out a laugh, “Are you saying that our bad boy Jackson is bottoming for puppy Isaac? Are you kidding me? This is epic! Are you sure we’re talking about the same Jackson? I mean Jackson, who is the school bully? The macho man? The I’m-Not-Showing-Any-Emotions Jackson? That’s…-“_ _

__Derek cut him off, “Stiles, shut up, they can hear you.”_ _

__“No they can’t. There’s not any noises coming, so they probably fell asleep already," Stiles kept laughing, "Oh, by the way Derek?”_ _

__“What?”_ _

__“Do you think I could top you someday?” Stiles asked innocently._ _

__Derek groaned as his dick twitched._ _

**Author's Note:**

> Hope you enjoyed! I have some plans for these little one shots so keep following my stories! :) 
> 
> Remember to leave comments and kudos, I live for them ;) ~


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